2021 Fiscal Year Final Research Report
Construction of asymmetric carbon using organo-catalyst and systematic synthetic studies on vibsane-type diterpenes
| Project/Area Number |
19K05488
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Review Section |
Basic Section 33020:Synthetic organic chemistry-related
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| Research Institution | Tokushima Bunri University |
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Principal Investigator |
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| Project Period (FY) |
2019-04-01 – 2022-03-31
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| Keywords | 有機触媒 / 有機化学合成 / 不斉アルドール反応 / ビブサン型ジテルペエン / スピロビブサニンA / [3.3.1]-ビシクロ骨格 |
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| Outline of Final Research Achievements |
In this study, I synthesized a key intermediate for vibsanins and examined a synthetic study on spirovibsanin A which is one of the vibsane-type diterpenes.
First, we developed an asymmetric aldol reaction using the organic catalyst Hua-cat, and began the synthesis of key intermediates common to vibsane-type diterpenes. As a result of investigating the reactions using various organic catalysts, it was found that Hua-cat having a dodecylphenylsulfonyl group exhibits high enantioselectivity. After examinations of the reaction conditions in detail, we succeeded in synthesizing the target key intermediate with 81% yield and 84% ee by adding TFA and using toluene as a solvent. Next, the synthetic study of siprovibsanin was conducted on the obtained key intermediate. Utilizing the [3.3.1]-bicyclo structure of the intermediate, two functional groups could be stereoselectively introduced, and the carbon skeleton of the natural product was successfully synthesized.
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| Free Research Field |
化学薬学
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| Academic Significance and Societal Importance of the Research Achievements |
神経栄養因子様活性を有するビブサン型ジテルペンは、アルツハイマー病治療薬のリード化合物として期待されている。しかし、ビブサニン類は天然から得られる量はごく微量であり、詳細な活性試験を実施するには化学合成による試料の供給が急務である。今回開発した合成法はビブサン型ジテルペンの一般的な合成法であり、これまでに活性が調べられていない化合物についても網羅的に合成し、活性試験に供与できるものである。また合成の初期段階で開発した不斉アルドール反応は種々の天然物にも応用可能と考えられ、有機合成化学の分野での強力なツールになると期待している。
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